A Simple Guide to Risk-Taking

“And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom.” ~Anais Nin

Would you consider yourself a risk-taker?

If you had asked me that question ten years ago, my answer would have been a resounding “no!”

I was too invested in the status quo, plus I had young children. I didn’t want to do anything that might disrupt them. (A very convenient excuse, wouldn’t you say?)

But in truth, I was simply afraid of risk.

I didn’t like the unknown. I didn’t feel comfortable with ambiguity and uncertainty. And I had a very imaginative way of picturing the most unpleasant outcomes to any risky decision or action. So I just avoided risk. Things were OK without it.

But taking a stance against risk means taking a stance against big opportunity and bold growth. That is the price of inner security. Any positive change, any personal evolution, any successful venture involves some element of risk.

People who have started new businesses, changed careers, gotten engaged, moved to a new city, written a book, started an exercise program, spoken to a stranger at a party, or traveled to a foreign country, have all accepted the chasm of risk that hovers between them and their goal or action.

Risk is sometimes a gaping gorge or it can be a narrow creek, but to the risk-taker, the width is never as scary as the perceived dark and bottomless depths of the abyss. What horrors lurk at the bottom if you start to cross over and fall?

skydiving people guide to risk taking

If you’ve taken some risks in your life, you have probably fallen into the depths of a failed risk a few times. After the experience of a falling, you learn that hitting the bottom is rarely as painful as you perceived it to be. Once you get up and dust yourself off, you may have a few bumps and bruises, but you realize you’re still alive. You haven’t been swallowed up by the thing you feared so much.

Of course, the bigger the risk, the more uncertainty and fear will be present for you. But it’s the big risks, the boldest moves, that often reap the greatest rewards. Very few things in life come with a guarantee. At some point, you must make the decision to either remain on the edge or take that leap of faith. It’s never easy, but there are ways to make it easier — and maybe even a little fun.

Here’s a little guidance to help you accept the inevitability of risk with change and growth, and to approach risk in a way that is thoughtful and realistic.


I always begin with awareness as a step in any new concept or strategy.  So many of us stay stuck in beliefs simply because we don’t know we have a choice. Often people avoid risk altogether, as I used to, because they believe the possible fallout if they fail will be too destructive to handle. And some people cling to the belief that every decision must feel 100% perfect before they will act. With risk, you win some and you lose some, and you won’t get a certified letter in advance from the Wizard of Oz  telling you the outcome. But if you approach risk intelligently, the odds usually fall in your favor, and the fallout is more manageable if you do fail. If you never approach risk at all, you will always stay where you are.

Related: 3 Fearless Decisions Critical To Your Happiness


Before you begin the real work of planning for a risky decision, start with a vision of the positive outcome you hope to achieve with the risk. This will create some excitement and energy around the risk to counter-balance your fears.  If you want to change jobs, visualize yourself in the perfect job you want. If you want to make a financial investment in a business, visualize your financial success and what you will do with the money. If you want to try skydiving, visualize yourself floating through the sky with an amazing view all around you, then landing safely. Write down your vision so you can refer to it through the process of planning your risky business.


Conduct whatever due-diligence is necessary for learning more about the decision or action you are considering. Read about it, learn what others have done, get the statistics, run the numbers, cover all of your bases to make sure you are completely and totally educated about this risk. Without this step, you double or triple your risk because you don’t have the facts. The bigger the risk, the more preparation you will need. Make notes about your findings.

Pros and Cons

Write down a list of the potential pros and cons of taking this risk. You may not be able to anticipate all of them, but based on your research, write down as many as you can. Next to the cons, write down your best guess on the percentage of likelihood for each con you list. Pay particular attention to those you list as 40% or higher. Are these cons you could cope with if they happened? How would you cope with them? In general, do the pros outweigh the cons? Is the likelihood of success more or less than the likelihood of failure?


Don’t go it alone. Seek out input from other people who are experts in this particular area and those whose opinion and wisdom you respect. Review your research and pros/cons with them. Talk through the possible outcomes and how you might handle a failed risk.

man doing line walk guide to risk taking

Take notes on what each person has to say about your risk. Weigh their advice against your own thoughts and feelings. If they present a valid argument one way or another, don’t dismiss it because it may not be what you want to hear.


If your risk might impact those close to you, especially a spouse and children, be sure you fully communicate your risky decision and share the research and feedback you’ve received. Family members can often fuel your fears because of their own fears at how your risk might impact them. In fact, they might outright reject your risk and initially refuse to participate or support it. Listen to their concerns mindfully, and do your best to address them. Most risky decisions must be made mutually by a married couple.  It might take the help and support of a coach or counselor to lead you both through this decision.


If there is a way to “try out” your risky action before you fully commit, then do so. Get a feel for what you are about to jump into. This provides further information for making a sound decision.

Related: 20 Actions To Take To Be Bold This Year


We tend to sell ourselves short when it comes to our inner wisdom, intuition, and intelligence. If you have done the due diligence and communicated fully, sit quietly with your risk and see what you feel compelled to do. Look back a past decisions you have made and the results of them. Are you happy with the way you handled those decisions? Did you do the necessary work and planning? You will never feel completely at ease with a risky decision, but you can feel a level of trust that you have done your best, as evidenced by past decisions and actions.


The day will come when there is nothing more to consider, no one else to talk to, nothing left to communicate. If your planning and preparation has come down on the side of taking the risk, then you must take the leap. You haven’t done all of this preparation work just to stand on the edge with your heart thumping like a kid on the end of a diving board for the first time. You’ve made the decision, so leap into it with a swan dive. Go for it with full gusto.

The greatest moment of risk-taking is the exhilarating moment immediately after taking it when you are no longer trapped by anxiety. You are in the air, between your angst-filled decision and the ultimate outcome. You’ve done it, and now you’re perfectly free in this moment. And you are potentially moving toward a wonderful, exciting new chapter of your life.

16 thoughts on “A Simple Guide to Risk-Taking”

  1. Great article Barrie!
    There was time when I wouln´t take any risk. I just liked to stay in my comfort zone with both feet on the ground. Then I said YES to some opportunities in my life and never looked back. From the next month on, I´m starting to study in another country not knowing anyone there. It´s a big challenge and quit a risk but I´m convinced that this will be a really great experience for me.
    Therefore, I would like to encourage everyone to take a risk from time to time!
    Thanks for sharing, Petra

    • Wow Petra! That is really brave. Have you moved there yet? Please keep us posted on how it’s going. 🙂

    • Thanks Barrie! No I haven´t moved yet. It´s planned for the beginning of October. Of course, I will keep you up tu date 🙂

  2. I love reading these articles. They give me motivation to get out of the situation that I am in. I have been with my employer for 5 years and the misery has completely changed me. There is nothing positive about this job but that i have a job and that i am truly grateful otherwise i dont know how i would feed my family. But it has been a mental, physical draining time for me. This place is far from a professional company, i guess because it is family owned and management does as they please with the employees since the owners have no time to be involved. I am constantly complaining about it but do nothing to get myself out. I have been applying places but no response and i dont know what i am doing wrong. Two of my colleagues have left me and i am truly having a hard time i want to cry sometimes. You will never understand until you have been in this situation. Please, any advice would help. Thanks

    • Hi Violet,
      I know how tough that situation can be. You feel completely trapped. Are you in a position to save any money? If so, start saving an emergency fund so that you have a cushion. Do you know what you want to do — the kind of job you want? If not, you might want to check out my passion course to help you sort through that. Is there any other kind of job outside of your field that you could take as an interim position while you seek the job you want? Set goals for yourself regarding your job search. Break down the job search tasks into small actions and write the actions necessary down on index cards. Pull one index card a day and do the action. Get yourself some gold stars and put them on your calendar for every day that you take the action. It’s silly, but you will love seeing those gold stars lined up! Make finding a job you love your priority now.

    • Yes, there is risk in everything — even in avoiding risk. The risk there is that you risk losing out on something wonderful!

  3. Hi Barrie,

    I guess I’ve been a risk taker as long as I can remember. As a R.E. agent, a stock broker, a home building consultant helping people “risk” building their own homes … I can’t remember the last “job” I had where I actually got paid rather than commissions or simply selling my own products or services.

    Yet, despite that, risking is still somewhat scary. And the steps you listed are so important. However, living with risk enhances the journey of life. The risk-reward scenario gives such good feedback and tells you what you’re doing right and wrong (even though both sides of that are right or good.)

    When you get down to it, not risking is just not living. Might as well get on to the next life! 😉

    (which we can start right now…)

    • Thank you for sharing your story Carmelo. Yes, you have been in some risky businesses, but you are so right — risk is our greatest teacher. It also puts us squarely at the peak experience of living. Putting ourselves out there and letting the chips fall as they may is exciting and scary — but less scary when you do it a few times.

  4. Hi Barrie:

    I took this sort of leap in 2010. I took a leap because I was stressed to the max at my job and I yearned to make lots of money, lots more then what I was making. I wanted to do work I enjoyed more and that would give me more ‘status’ in the work community in which I existed.

    Everything went wrong. I will spare you the details but the end result was not the bliss I had hoped for and expected. Lots of other stuff went horribly wrong as well in 2010. The new position ended in a very short time by my own decision.

    After a period of self-pity and intense feelings of mortification, I found what I expected to be a great job. This job also ended after a short time and not in a way that brought me happiness. After this job ended (and actually before as I had some notice about my impending demise with the company) I found the job I now hold with a great company.

    Am I glad I took the leap? If I could have seen the future, I would still be with my old company somewhat safe but still stressed and unhappy (maybe, who knows? Its all conjecture, that part of my life is all over). Am I in a better place now? Yes, money-wise but I find myself afraid all the time that the other shoe will drop and I will be told I am not good enough or some other catastrophe will occur and I will be out in the cold (figuratively and quite possible literally should the worst happen) once again.

    I hope everyone CAREFULLY considers before they go off making big leaps. They do not always go the way it tells in fairy tales.

    But sometimes it does go well, just look before you leap!

  5. Great article. After having climbed mountains in the Himalayas, skied across Greenland, served six years in the Marines and started two business, I can honestly say fear is the best friend you will ever have. Every one of those things scared me, but outside our comfort zone lies infinite possibility. Like I say on my site, success lies just one inch beyond your limits, you just gotta take that inch outside of what you know and into that unknown. Love how you broke down the steps to make it easy to take that leap. Awesome work!


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